Winning the Right Deals with Matt Carey | Coach2Scale Episode #83
Every sales leader has heard the mantra: “Pipeline cures all.” But what if that’s only half the truth? In this episode, Matt Carey, SVP of Global Sales at FIS, breaks down why more pipeline isn’t always the answer—the right pipeline is. He shares hard-earned lessons from leading sales teams at Oracle, SAP, and FIS, explaining how top-performing organizations prioritize quality over quantity, measure pipeline health beyond raw coverage, and avoid common forecasting pitfalls.
Matt also explores the real role of frontline managers, not as super reps, but as force multipliers who elevate their teams. He discusses hiring strategies that separate true performers from resume fluff, the importance of post-mortem loss reviews, and why most companies still get coaching wrong. Whether you're a CRO, VP of Sales, or a frontline manager looking to level up, this conversation is packed with insights that will change the way you build and manage your pipeline.
Top Takeaways:
- Pipeline Quantity vs. Quality – More pipeline doesn’t guarantee success; leaders must focus on the right pipeline by assessing deal quality, aging, and true viability.
- The Problem with "Just Add More Pipeline" Thinking – Sales teams often flood CRMs with unqualified deals to meet coverage targets, leading to bloated and misleading forecasts.
- Why Frontline Managers Must Stop Being Super Reps – The best managers don’t just close deals for their teams; they enable reps to develop the skills to win consistently.
- Hiring Based on Past Performance, Not Promises – Great sales hires have a history of winning, regardless of industry or background; track record matters more than potential.
- Loss Reviews Are More Valuable Than Win Reviews – Studying why deals were lost provides deeper insights into messaging gaps, pricing misalignment, and product fit issues.
- How Sales Leaders Sell Internally – At higher levels, sales leaders spend as much time selling internally for budget, resources, and strategy alignment as they do selling to customers.
- Coaching Needs a System, Not Just Good Intentions – Too many one-on-ones are either deal reviews or therapy sessions; real coaching needs structure, accountability, and a focus on skill development.
- Managing a Global Sales Team Requires Cultural Awareness – Sales leaders must adapt their messaging and approach across markets, respecting regional differences in business etiquette and buying behavior.
- The Shift from Tactical to Strategic Leadership – Senior sales leaders must move beyond the day-to-day deal cycle and focus on long-term market positioning, competitive threats, and team scalability.
- Why Sales Leaders Must Track Trends, Not Just Deals – The best leaders analyze broader win-loss data, competitive shifts, and industry changes to refine strategy, not just react to individual deal outcomes.
Ways to Tune In:
- Spotify: https://open.spotify.com/show/0Yb1wPzUxyrfR0Dx35ym1A
- Apple Podcasts: https://podcasts.apple.com/us/podcast/coach2scale-how-modern-leaders-build-a-coaching-culture/id1699901434
- Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2NvYWNoMnNjYWxlLWhvdy1tb2Rlcm4tbGVhZGVycy1idWlsZC1hLWNvYWNoaW5nLWN1bHR1cmU
- Amazon Music: https://music.amazon.com/podcasts/fd188af6-7c17-4b2e-a0b2-196ecd6fdf77
- Podchaser: https://www.podchaser.com/podcasts/coach2scale-how-modern-leaders-5419703
- YouTube: https://www.youtube.com/@Coach2Scale
CoachEm™ is the first Coaching Execution Platform that integrates deep learning technology to proactively analyze patterns, highlight the "why" behind the data with root causes, and identify the actions that will ultimately improve business results going forward. These practical coaching recommendations for managers will help their teams drive more deals, bigger deals, faster deals, and loyal customers. Built with decades of go-to-market experience, world-renowned data scientists, and advanced causal AI/ML technology, CoachEm™ leverages your existing tech stack to increase rep productivity, increase retention, and replicate best practices across your team.
Learn more at coachem.io
